TWI433894B - 苝顏料之水性合成 - Google Patents

苝顏料之水性合成 Download PDF

Info

Publication number: TWI433894B
Authority: TW; Taiwan
Prior art keywords: reaction; methyl; pigment; butenyl; tertiary amine
Prior art date: 2007-07-03

Application number

TW097124933A

Other languages

English (en)

Chinese (zh)

Other versions

TW200920793A (en

Inventor

Johannes Loebel

Andreas Stohr

Original Assignee

Basf Se

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-07-03

Filing date

2008-07-02

Publication date

2014-04-11

2008-07-02 Application filed by Basf Se filed Critical Basf Se

2009-05-16 Publication of TW200920793A publication Critical patent/TW200920793A/zh

2014-04-11 Application granted granted Critical

2014-04-11 Publication of TWI433894B publication Critical patent/TWI433894B/zh

Links

239000000049 pigment Substances 0.000 title claims abstract description 58
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title abstract 2
CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title abstract 2
230000015572 biosynthetic process Effects 0.000 title description 5
238000003786 synthesis reaction Methods 0.000 title description 4
238000006243 chemical reaction Methods 0.000 claims abstract description 34
239000000203 mixture Substances 0.000 claims abstract description 23
150000003335 secondary amines Chemical class 0.000 claims abstract description 20
150000003512 tertiary amines Chemical class 0.000 claims abstract description 20
239000012431 aqueous reaction media Substances 0.000 claims abstract description 14
150000004984 aromatic diamines Chemical class 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 52
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 25
150000004056 anthraquinones Chemical class 0.000 claims description 25
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
239000003960 organic solvent Substances 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical group CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 claims description 4
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 4
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 claims description 2
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 2
239000011149 active material Substances 0.000 claims description 2
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
125000005427 anthranyl group Chemical group 0.000 claims description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 abstract description 4
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract description 2
125000004957 naphthylene group Chemical group 0.000 abstract 1
WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 abstract 1
125000005551 pyridylene group Chemical group 0.000 abstract 1
-1 hafnium halide Chemical class 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
239000000463 material Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000000725 suspension Substances 0.000 description 15
125000003118 aryl group Chemical group 0.000 description 12
229920001577 copolymer Polymers 0.000 description 12
229920003023 plastic Polymers 0.000 description 11
239000004033 plastic Substances 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 8
150000004985 diamines Chemical class 0.000 description 8
238000001035 drying Methods 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000002585 base Substances 0.000 description 6
229910052797 bismuth Inorganic materials 0.000 description 6
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
229920000570 polyether Polymers 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
150000000000 tetracarboxylic acids Chemical class 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000000460 chlorine Chemical group 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
125000001624 naphthyl group Chemical group 0.000 description 5
229920000098 polyolefin Polymers 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003466 welding Methods 0.000 description 5
YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
239000004721 Polyphenylene oxide Substances 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
239000011368 organic material Substances 0.000 description 4
229920000139 polyethylene terephthalate Polymers 0.000 description 4
239000005020 polyethylene terephthalate Substances 0.000 description 4
238000012545 processing Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
239000004677 Nylon Substances 0.000 description 3
239000004743 Polypropylene Substances 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
238000004040 coloring Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
229910010272 inorganic material Inorganic materials 0.000 description 3
239000011147 inorganic material Substances 0.000 description 3
229920001778 nylon Polymers 0.000 description 3
239000002245 particle Substances 0.000 description 3
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 3
229920001707 polybutylene terephthalate Polymers 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
239000011164 primary particle Substances 0.000 description 3
238000012958 reprocessing Methods 0.000 description 3
229910052707 ruthenium Inorganic materials 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
239000001993 wax Substances 0.000 description 3
125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
229930040373 Paraformaldehyde Natural products 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000001000 anthraquinone dye Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000000975 dye Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
239000000976 ink Substances 0.000 description 2
238000009413 insulation Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
239000006069 physical mixture Substances 0.000 description 2
229920000233 poly(alkylene oxides) Polymers 0.000 description 2
239000004417 polycarbonate Substances 0.000 description 2
229920000515 polycarbonate Polymers 0.000 description 2
229920002098 polyfluorene Polymers 0.000 description 2
229920002959 polymer blend Polymers 0.000 description 2
229920000193 polymethacrylate Polymers 0.000 description 2
229920006324 polyoxymethylene Polymers 0.000 description 2
229920001343 polytetrafluoroethylene Polymers 0.000 description 2
239000004810 polytetrafluoroethylene Substances 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
229920002981 polyvinylidene fluoride Polymers 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000006079 1,1,2-trimethyl-2-propenyl group Chemical group 0.000 description 1
125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 1
125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000006061 1,2-dimethyl-1-butenyl group Chemical group 0.000 description 1
125000006034 1,2-dimethyl-1-propenyl group Chemical group 0.000 description 1
125000006062 1,2-dimethyl-2-butenyl group Chemical group 0.000 description 1
125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
125000006073 1-ethyl-1-butenyl group Chemical group 0.000 description 1
125000006080 1-ethyl-1-methyl-2-propenyl group Chemical group 0.000 description 1
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125000006082 1-ethyl-2-methyl-2-propenyl group Chemical group 0.000 description 1
125000006037 1-ethyl-2-propenyl group Chemical group 0.000 description 1
125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
125000006039 1-hexenyl group Chemical group 0.000 description 1
125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
125000006044 1-methyl-1-pentenyl group Chemical group 0.000 description 1
125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
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125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
125000006023 1-pentenyl group Chemical group 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
125000006067 2,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
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125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000006076 2-ethyl-1-butenyl group Chemical group 0.000 description 1
125000006077 2-ethyl-2-butenyl group Chemical group 0.000 description 1
125000006078 2-ethyl-3-butenyl group Chemical group 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006040 2-hexenyl group Chemical group 0.000 description 1
125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 1
125000006045 2-methyl-1-pentenyl group Chemical group 0.000 description 1
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
125000006056 2-methyl-4-pentenyl group Chemical group 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
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125000006072 3,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
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PPAULTVPKLVLII-UHFFFAOYSA-N 4,5-diaminopyrimidine Chemical compound NC1=CN=CN=C1N PPAULTVPKLVLII-UHFFFAOYSA-N 0.000 description 1
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239000002841 Lewis acid Substances 0.000 description 1
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239000012876 carrier material Substances 0.000 description 1
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150000001880 copper compounds Chemical class 0.000 description 1
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125000004122 cyclic group Chemical group 0.000 description 1
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229920000831 ionic polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
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JHDZTRVDWDZIBI-UHFFFAOYSA-N isoquinoline-1,8-diamine Chemical compound C1=NC(N)=C2C(N)=CC=CC2=C1 JHDZTRVDWDZIBI-UHFFFAOYSA-N 0.000 description 1
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238000004898 kneading Methods 0.000 description 1
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239000007791 liquid phase Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
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150000005309 metal halides Chemical class 0.000 description 1
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238000003801 milling Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
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239000002736 nonionic surfactant Substances 0.000 description 1
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150000007524 organic acids Chemical class 0.000 description 1
239000012860 organic pigment Substances 0.000 description 1
YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 description 1
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GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
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150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000002464 physical blending Methods 0.000 description 1
CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
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229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
229920001643 poly(ether ketone) Polymers 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000412 polyarylene Polymers 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000011112 polyethylene naphthalate Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920001955 polyphenylene ether Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
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239000011118 polyvinyl acetate Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920001290 polyvinyl ester Polymers 0.000 description 1
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229940072033 potash Drugs 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
229920001384 propylene homopolymer Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
NYDAOEQPKZSNOI-UHFFFAOYSA-N quinoline-4,5-diamine Chemical compound C1=CC(N)=C2C(N)=CC=CC2=N1 NYDAOEQPKZSNOI-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000003980 solgel method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Paints Or Removers (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Compositions Of Macromolecular Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW097124933A 2007-07-03 2008-07-02 苝顏料之水性合成 TWI433894B (zh)

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EP (1)	EP2176356B1 (de)
JP (1)	JP5447865B2 (de)
KR (1)	KR101542263B1 (de)
CN (1)	CN101688063B (de)
AT (1)	ATE546493T1 (de)
ES (1)	ES2381058T3 (de)
TW (1)	TWI433894B (de)
WO (1)	WO2009003980A2 (de)

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WO2010049382A1 (de) *	2008-10-27	2010-05-06	Basf Se	Verfahren zur herstellung einer suspension nanopartikulärer metallboride
CN105694531B (zh) *	2016-03-25	2017-10-27	电子科技大学	一种苝系颜料制备方法
KR102836965B1 (ko) *	2019-05-15	2025-07-22	엠. 테크닉 가부시키가이샤	페릴렌계 흑색 안료 미립자, 그 제조 방법, 그것을 포함하는 흑색 안료 조성물, 및 색상 및/또는 채도가 제어된 페릴렌계 흑색 안료 미립자의 제조 방법
CN116761854A (zh) *	2020-12-21	2023-09-15	太阳化学有限公司	近红外(nir)透明中性黑固溶体颜料
EP4263723A1 (de)	2020-12-21	2023-10-25	Sun Chemical B.V.	Transparente neutrale schwarze perylen-festlösungen im nahen infrarotbereich (nir)
WO2025031982A1 (en)	2023-08-04	2025-02-13	Sun Chemical B.V.	Perylene black pigments with enhanced near-infrared-transparency properties
WO2025237878A1 (en)	2024-05-13	2025-11-20	Sun Chemical B.V.	Low bleeding perylene black pigments and process for producing the same
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2008
- 2008-06-30 AT AT08774532T patent/ATE546493T1/de active
- 2008-06-30 ES ES08774532T patent/ES2381058T3/es active Active
- 2008-06-30 CN CN200880023188.4A patent/CN101688063B/zh active Active
- 2008-06-30 KR KR1020107001605A patent/KR101542263B1/ko active Active
- 2008-06-30 WO PCT/EP2008/058378 patent/WO2009003980A2/de not_active Ceased
- 2008-06-30 US US12/667,334 patent/US8334386B2/en active Active
- 2008-06-30 EP EP08774532A patent/EP2176356B1/de active Active
- 2008-06-30 JP JP2010513957A patent/JP5447865B2/ja active Active
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Publication number	Publication date
TW200920793A (en)	2009-05-16
WO2009003980A3 (de)	2009-08-06
CN101688063A (zh)	2010-03-31
KR20100028650A (ko)	2010-03-12
ATE546493T1 (de)	2012-03-15
CN101688063B (zh)	2013-04-10
EP2176356B1 (de)	2012-02-22
EP2176356A2 (de)	2010-04-21
WO2009003980A2 (de)	2009-01-08
JP5447865B2 (ja)	2014-03-19
JP2010531906A (ja)	2010-09-30
ES2381058T3 (es)	2012-05-22
US20100184983A1 (en)	2010-07-22
US8334386B2 (en)	2012-12-18
KR101542263B1 (ko)	2015-08-06

Publication	Publication Date	Title
TWI433894B (zh)	2014-04-11	苝顏料之水性合成
EP2235112B1 (de)	2014-03-12	Synthese von farbmitteln in mischapparaturen
KR101153135B1 (ko)	2012-06-11	블랙 페릴렌 안료
TWI344977B (en)	2011-07-11	Compositions
JPH03181567A (ja)	1991-08-07	複素環族化合物
CN1527864A (zh)	2004-09-08	二萘嵌苯颜料组合物
JP2011190449A (ja)	2011-09-29	有機顔料の調整法
DE69121436T2 (de)	1997-01-09	Organische Materialien, die sulfonamidogebundene Poly(oxyalkylen)gruppen tragen und ihre Herstellung
JP3897374B2 (ja)	2007-03-22	３、６−ジ（４−ビフェニル）−１、４−ジケト−ピロロ［３、４−ｃ］−ピロールをベースとした顔料組成物
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JP2004083673A (ja)	2004-03-18	プラスチック用着色剤およびその使用
WO2025237878A1 (en)	2025-11-20	Low bleeding perylene black pigments and process for producing the same
DE102004057876A1 (de)	2006-06-01	Schwarze Perylenpigmente
JP2004083675A (ja)	2004-03-18	プラスチック用着色剤およびその使用
JPS5823840A (ja)	1983-02-12	ポリオレフイン用着色剤
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